Hydrochloric Acid → Ethyl 7-(cyano-ethoxycarbonyl-methyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate

HRID 1032015Notes

Reaction equation

HRID 1032015 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.[C:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])#[N:23].[H-].[Na+].Cl>O.O1CCOCC1>[C:22]([CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:11]1[CH:12]=[C:13]2[C:8]([C:7](=[O:16])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][N:4]2[CH:1]2[CH2:3][CH2:2]2)=[CH:9][C:10]=1[F:15])#[N:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 9817544Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 14422910Ethyl 7-(cyano-ethoxycarbonyl-methyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

8.8 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate and 5.1 g of ethyl cyanoacetate are initially introduced into 120 ml of dioxane. 1.74 g of NaH are added in portions. The mixture is then boiled for 3 hours, diluted with water and rendered acidic using HCl. It is extracted using methylene chloride. The organic phase is dried and concentrated. The residue is recrystallized from ethanol.

Workup

  1. extractionIt is extracted
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-d94367b147c9428c820b175f9eb184d7
Source dataset
uspto-grants-1990_09
Patent number
US04956465

Reaction notes

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